Creation: Appeared July 1935 as a renumbering of a large chunk of VA 5 running generally as it does now. It eastern end was at 2nd St at Broad, where it ran into US 60.
Adjustments: In Oct 1935 (CTB), US 250 was rerouted in Charlottesville. Initially it used Main St, then EB 5th and WB 2nd, Jefferson St, Park St, High St (also partly Free Bridge Rd then). With this change, US 250 used Main St, then EB Water/2nd and WB 1st, High St, Locust Ave, and Watson St/Long Ave (this is now part of the 250 bypass).
In Sept 1937 (CTB), US 250 was put on new routing west of Ivy, leaving behind SRs 738 and 739 (now partly SR 786).
In 1938, US 250 was rerouted between Churchville and Staunton onto
its current path. US 250 originally used the SR 840 loop, then used SR
721 south a bit, crossed Middle River, then used SR 722 north back to
current US 250.

US 250 all over the place
1936 Augusta County

US 250 rebuilt
1958 Augusta County

In May 1939 (CTB), The Route 250 Association requested that US 250
be extended along US 60 east to Old Point Comfort. There was no
decision given on that in the CTB but this did not ever happen.
US 250 had a gap in it at Shadwell. To connect, one had to use VA
22 to SR 729 (no longer connects to VA 22) south to SR 731 east to US
250. The gap was closed about 1939 with US 250's current bridge over
the railroad at Shadwell.

US 250 gap at Shadwell
1936 Albemarle County

US 250 continuous
1958 Albemarle County

Sometime in the late 30s, US 250 was given its current routing just west of US 29, leaving behind SR 601/754.
In Jan 1941 (CTB), US 250 was given its current routing bypassing the village of Afton, leaving behind SR 750 and a bit of VA 151 (now VA 6).
In Nov 1942 (CTB), US 250 was removed from Crozet and placed on its current bypass there. This was a replacement of VA 240. The E-W part of the old route became VA 240 and the N-S piece became VA 230 (now also VA 240).

US 250 through Crozet
1936 Official

US 250 bypasses Crozet
1944 Official

In Sept 1945 (CTB), US 250 was removed from SR 796 in western
Albemarle County. Also, US 250 bypassed Yancey Mills, leaving behind SR
797.
In Nov 1948 (CTB), US 250 was rerouted within Charlottesville.
In
this change, WB now used High/Preston/Grady/Rugby/Main (this is still
WB US 250 Business' route). EB now used Main/Water/7th/High.
Between 1955-58, US 250 was moved to its bypass of central Waynesboro, replacing US 250-A. The old route on Main St remained US 340.
About 1969, US 250 was placed on its current Charlottesville Bypass
replacing US 250-A. US 250 through Charlottesville became US 250
Business (EB has been rerouted since).

US 250 initial C'ville route (shown as then-VA 5)
1933 Official

US 250 loops up on Locust east of Downtown
1945 Albemarle County

US 250 wide splits in C'ville
1958 Albemarle County

US 250 bypasses C'ville
1970 Official

In June 1974 (CTB), US 250 was extended east along Broad St replacing US 60 to end at 21st St which is where US 60 now met Broad.
In Sept 2003 (CTB), US 250 east was truncated to US 360 when US 60 was removed from Broad St altogether.
Improvements: Upon designation, US 250 was paved everywhere except WV Line to Monterey.
US 250 was paved west of Monterey in 1939.
The first multilaning of US 250 occurred by 1954, on Broad St out to Staples Mill Rd
In 1958, 4-laning was extended west to Dickens Rd
In 1969, US 250 was 4-laned from US 29 east to just short of US 250 bus/VA 20 when it was placed on the Charlottesville Bypass.
In 1970, US 250 was widened from SR 654 Barracks Rd to US 29; Broad St was 4-laned out to Glenside Dr.In 1972, US 250 was 4-laned from US 250 Bus west of Charlottesville halfway to SR 654 Barracks Rd
In 1975, US 250 was multilaned the rest of the way between US 250 bus and SR 654.
In 1978, US 250 was multilaned around the I-64 Short Pump area
In 1979, US 250 Broad St was 4-laned from Glenside Dr to Parham Rd.
In 1983 or 1984, US 250 Broad St was 4-laned from Parham Rd to VA 157.
In 1988, US 250 was widened from Staunton to Waynesboro
In 1992, US 250 was 4-laned from VA 157 west to I-64 Short Pump
In 1993, US 250 was 4-laned from I-64 Shadwell west to Locust Ave
(Charlottesville Bypass now all 4-laned, even though officials all
through the 1970s showed this erroneously).
In 1997 or 1998, US 250 was widened from I-64 Short Pump west to the Goochland Line.
In 2003 (bridge date...still not shown on officials), US 250 was multilaned from the Henrico-Goochland Line west to SR 623
US 250 has substantial sections of 6 or more lanes: VA 288 east to downtown Richmond
Posted: Fully posted; Cutouts in Staunton and Highland County still plentiful into 2013; Richmond cutouts went away in mid-2000s.
In the late 1990s there was an error VA 250 shield WB leaving VA 157.
US 250 is poorly posted east of US 1-301 and back to at least 1981 is not posted east of I-95.
Multiplexes: VA 42 (0.47 mi)
US 11 Bus (0.76 mi)
US 11 (0.07 mi)
US 340 (0.19 mi)
US 29 (2.21 mi)
VA 20 (0.26 mi)
US 33 (3.06 mi)
Legislative names: The Jefferson Hwy, from Staunton to
Shadwell except not Charlottesville Bypass (3/9/22 designation predates
US 250); The Woodrow Wilson Pkwy, from ECL Staunton to the Blue Ridge
Pkwy (since 2/28/66); Other names: Highland Tpk (Highland Co); Hankey Mtn
Hwy (Highland Line to Churchville); Churchville Ave (Churchville to
Staunton); Augusta St/Johnson St/Greenville Ave/Richmond Rd (Staunton);
Main St/Broad St (Waynesboro); Rockfish Gap Tpk (Blue Ridge Pkwy to
Mechum River); Ivy Rd (VA 240 to US 29); Monacan Trail Rd (US 29
duplex); Long St (Charlottesville); Richmond Rd (Albemarle Co east of
Charlottesville, Fluvanna Co); Three Notch Rd (w Louisa Co segment);
Broad Street Rd (Goochland Co, E Louisa Co segment); Broad St (Henrico
Co, Richmond)
Scenic Byway: Blue Ridge Pkwy to US 29/250 Bus (12/17/83)
Truck Route: A posted truck route for Staunton appeared
about 1999. Runs from US 250 along VA 261 to US 11 north to VA 262 west
back around to US 250 west of Staunton. It is very well posted.
Comment: US 250 is kind of a forgotten highway in most
parts of Virginia. It is closely paralleled by I-64 from Staunton to
Richmond and west of Staunton runs through pretty unpopulated
territory.
US 250 is however a wonderful, peaceful drive when not in the
cities. West of Staunton it is quite scenic, especially in Highland
County.
US 250 has several mountain range crossings west of Staunton. The
worst is at the Augusta-Highland Line but the others are not all that
bad. The crossing at Afton Mtn can actually be driven at 55 mph.
VDOT Traffic logs back to at least 2001 say that US 250 is on
split streets in downtown Staunton, with WB using New St. However, US
250 is not posted this way in the field.
US 250 is misidentified as VA 5 in both the Staunton and Charlottesville insets of the 1936 Official.

From:
near Charlottesville (Albemarle County)To:
near City of Charlottesville Total Length: 4.55 miles

Creation: Designated about 1969 as a renumbering of mainline US
250 through Charlottesville. Westbound US 250 Business runs the way it
did from the beginning. Eastbound started out using Main St-Water
St-7th St-High St Adjustments: About 1975, US 250 Bus EB was rerouted to use 9th St between Main St and High St
About 1977, US 250 Bus EB was rerouted again to use its current routing: Main-McIntire-Market-9th-High.
Improvements: Paved upon inception;
EB is multilaned on McIntire and 9th Sts
WB is multilaned on Preston Av from McIntire to Rosser.
Although US 250 Business is on "one-way splits" for a large chunk
of its route, the streets are actually 2-way traffic on 2-lane roads.
Posted: Fully posted
Multiplexes: VA 20 (1.01 mi)
Legislative names: Jefferson Highway (entire route)
Other names: The parts that are not in the one-way split:
Ivy Rd/University Ave/High St
Scenic Byway: no segments
Comment: US 250 Business passes through part of the University of Virginia campus.

US 250 Bus initial route
1970 Official

EB moves from 7th to 9th
1975 Official

EB moves to current route
1990 Official

US 250 ALT not currently assigned

Previous US 250 ALT's:

US 250 ALT #1: First appeared in the May 1952 CTB minutes
as the route designation for the Charlottesville Bypass, which is shown
as open from US 29 east to US 250/VA 20 beginning with the 1955
Official.
In 1961, US 250-A was extended west as new construction around to meet US 250, forming a complete bypass.
About 1969, US 250-A became mainline US 250.

US 250-A appears
1955 Official

US 250-A extended west
1961 Official

US 250 ALT #2: Appears in the CTB minutes in 1955 and
1960 as the bypass of central Waynesboro. The bridge over South River
is dated 1956 and the 1958 Augusta County map shows it as mainline US
250. To this point it is unclear if this was ever labeled on a map or
signed as US 250-A.